McCartney had a three-year relationship with Dot Rhone in Liverpool, buying her a gold ring in Hamburg. In London, McCartney had a five-year relationship with Asher, living in her parents' house for three years. He wrote several songs at the Ashers' house, including "Yesterday". Asher inspired other songs, such as "And I Love Her", "You Won't See Me" and "I'm Looking Through You". On 25 December 1967 they announced their engagement, but separated in early 1968. McCartney met American photographer Linda Eastman in a club in London while still with Asher. They met again at the launch party for the Beatles' Sgt. Pepper album. In May 1968, McCartney met Eastman again in New York, and they were married on 12 March 1969. They had three children together, and remained married until her death from breast cancer in 1998.

McCartney appeared publicly beside Heather Mills at a party in January 2000, to celebrate her 32nd birthday. On 11 June 2002, they were married at Castle Leslie in Glaslough, Ireland. They had one child, Beatrice, in 2003, but were living apart by May 2006. In July 2006, British newspapers announced that McCartney had petitioned for divorce. On 17 March 2008, the financial terms of the divorce were finalised, which awarded Mills £24.3 million ($38.5 million). In November 2007 McCartney started dating Nancy Shevell, who is a member of the board of the New York Metropolitan Transportation Authority, as well as vice president of a family-owned New England Motor Freight. It was announced on 6 May 2011 that the two had become engaged, and they married in London on 9 October 2011.

One of McCartney's first girlfriends, in 1959, was called Layla; a name he remembered as being unusual in Liverpool at the time.[1] She was slightly older than McCartney and used to ask him to baby-sit with her. Julie Arthur, another girlfriend, was Ted Ray's niece.[1]

McCartney's first serious girlfriend in Liverpool was 17-year-old Dorothy "Dot" Rhone (a bank clerk or a cashier at a chemist's, according to varying accounts),[2] whom he had met at The Casbah Club in 1959.[3][4] McCartney picked out the clothes he liked Rhone to wear and told her which make-up to use, also paying for her to have her blonde hair done in the style of Brigitte Bardot, whom both he and John Lennon idolised.[5] He disliked Rhone seeing her friends, and stopped her from smoking, even though he did so himself.[6] When McCartney first went to Hamburg with The Beatles he wrote regular letters to Rhone, and she accompanied Lennon's girlfriend, Cynthia Lennon to Hamburg when the group played there again in 1962.[7] According to Rhone, McCartney bought her a gold ring in Hamburg, a leather skirt, took her sightseeing, and was very attentive and caring.[8][9] For the time Rhone was there, the couple lived in a bungalow by the Hamburg docks that belonged to Rosa, a former cleaner at the Indra club.[10] McCartney admitted that he had other girlfriends in Hamburg when Rhone was in Liverpool,[6] admitting that they were usually "strippers," who knew a lot more about sex than Liverpool girls.[11]

Rhone later rented a room in the same house as Cynthia Lennon was living,[12] with McCartney contributing to the rent.[13] Shortly after McCartney returned from Hamburg in May 1962, Rhone told him that she was pregnant. They told McCartney's father, Jim McCartney, whom they expected to be shocked at the news, but found him delighted at the prospect of becoming a grandfather. McCartney took out a marriage licence and set the wedding date for November, shortly before the baby was due.[14] Rhone had a miscarriage in July 1962, and after a few weeks, McCartney's feelings towards Rhone "cooled off", and he finished their relationship.[15]

He then had a brief relationship with Thelma Pickles, who had previously dated Lennon. She later married Liverpool poet Roger McGough, but remembered McCartney as growing from a "plump young schoolboy into someone very much his own person" during their time together.[16] McCartney also had a stormy "on-off" relationship with Iris Caldwell, the younger sister of singer Rory Storm, who refused to bow to McCartney's demands.[6] After one argument, Caldwell poured a bowl of sugar over his head, but when McCartney turned up the next day, she had to phone her new boyfriend, George Harrison, to cancel their date.[17]

Rhone later emigrated to Toronto, Canada,[18] and McCartney met her again when the Beatles played there, and then again with Wings.[19] Rhone later said that "Love of the Loved" and "P.S. I Love You" were written about her.[20] Years later, Cynthia Lennon gave back to Rhone the gold ring that McCartney had bought her in Hamburg, having once tried it on while Rhone was washing dishes, and forgotten to take it off. Rhone is now a grandmother and lives in Mississauga, Ontario.[19]

McCartney first met British actress Jane Asher on 18 April 1963, when the Beatles performed at the Royal Albert Hall, in London, after a photographer asked them to pose with her.[21] They were then interviewed by Asher for the BBC, with Asher being photographed screaming at them like a fan.[22] McCartney soon met Asher's family: Margaret, her mother, who combined her life as the mother of three children with a full-time career as a music teacher, and Asher's father, Richard, who was a physician.[23] Her brother, Peter, was a member of Peter and Gordon, and her younger sister, Clare, was also an actress.[24] McCartney later gave "A World Without Love" to Peter and Gordon, as well as "Nobody I Know". Both songs were hits for the duo.[25] McCartney took up residence at the Ashers' house at 57 Wimpole Street, London, and lived there for nearly three years.[26] During his time there McCartney met writers such as Bertrand Russell, Harold Pinter, and Len Deighton.[27] He wrote several songs at the Ashers', including "Yesterday", and worked on songs with Lennon in the basement music room. Asher inspired many songs, such as "And I Love Her", "You Won't See Me", and "I'm Looking Through You".[28]

On 13 April 1965, McCartney bought a £40,000 three-storey Regency house at 7 Cavendish Avenue, St. John's Wood, London, and spent a further £20,000 renovating it.[29] He thanked the Ashers by paying for the decoration of the front of their house.[30] On 15 May 1967, McCartney met American photographer Linda Eastman at a Georgie Fame concert at The Bag O'Nails in London.[31][32] Eastman was in the UK on an assignment to take photographs of "swinging sixties" musicians in London.[33] They met again four days later at the launch party for the Sgt. Pepper album at Beatles' manager Brian Epstein's house in Belgravia, but after her assignment was completed, she flew back to New York.[34] On 25 December 1967, McCartney and Asher announced their engagement, and she accompanied McCartney to India in February and March 1968.[35]

Asher broke off the engagement in early 1968, after coming back from an acting assignment in Bristol to find McCartney in bed with another woman, Francie Schwartz. McCartney and Asher later attempted to mend their relationship, but finally broke up in July 1968. Asher has consistently refused to publicly discuss that part of her life.[36][37] Schwartz, a 23-year-old New York scriptwriter, had travelled to London trying to interest Apple Corps in a film script.[38] Schwartz was then asked by McCartney to move into his Cavendish Avenue house, and was given a job working for Derek Taylor at Apple,[39] which was then based in Wigmore Street, London.[40] She attended many sessions during the recording of the White Album, and was living with McCartney when Lennon and Yoko Ono were also invited to live there.[41] Shortly after, Schwartz sold the story of her time at Cavendish Avenue to Rolling Stone magazine.[42]

In May 1968, McCartney met Eastman again in New York, when Lennon and McCartney were there to announce the formation of Apple Corps.[43] In September, McCartney phoned her and asked her to fly over to London.[44] Six months later they were married at a small civil ceremony—when Eastman was four months pregnant with their child, Mary McCartney—at Marylebone Registry Office on 12 March 1969. He later said that his wife was the woman who "gave me the strength and courage to work again", after the break-up of the Beatles.[45] McCartney adopted her daughter from her first marriage, Heather, and had three children together: Mary, Stella, and James McCartney.[46] McCartney taught Linda to play keyboards, and permanently included her in the line-up of Wings.[47]

Linda died of breast cancer at age 56 in Tucson, Arizona, on 17 April 1998;[48] McCartney denied rumours that her death was an assisted suicide.[48][49] Along with eight other British composers, he contributed to the choral album A Garland for Linda, and dedicated his classical album, Ecce Cor Meum, to his late wife.[50] McCartney has said that he and Linda spent less than a week apart during their entire marriage, excluding McCartney's incarceration in Tokyo on drug charges in January 1980.[51]

After having sparked the interest of the tabloids about his appearances with Mills at events, McCartney appeared publicly beside Mills at a party in January 2000, to celebrate her 32nd birthday.[52] On 11 June 2002, McCartney married Mills, a former model and amputee campaigner against landmines, in an elaborate ceremony at Castle Leslie in Glaslough, County Monaghan, Ireland, where more than 300 guests were invited and the reception included a vegetarian banquet.[53] On 28 October 2003,[54] Mills gave birth to a daughter, Beatrice Milly McCartney, although the date has also been stated as 30 October.[55] The baby was reportedly named after Mills' mother Beatrice, and McCartney's Aunt Milly.[56]

On 29 July 2006, British newspapers announced that McCartney had petitioned for divorce, which sparked a media furore.[57][58] On 17 March 2008, the financial terms of the divorce were finalised,[59] with a settlement awarding Mills £24.3 million ($38.5 million).[60] The settlement stated that McCartney pay their four-year-old daughter Beatrice's nanny, school fees, and pay Beatrice £35,000 ($70,000) a year until she is 17, or ends her secondary education.[59] After the divorce ruling, Justice Bennett said that throughout the case Mills was "inconsistent, inaccurate and less than candid" while McCartney was "honest."[61][62] On 12 May 2008, Justice Hugh Bennett issued a decree nisi, which would become final after a period of six months apart.[63]

McCartney started dating Shevell in November 2007. She is a member of the board of the New York Metropolitan Transportation Authority as well as vice president of a family-owned transportation conglomerate that includes New England Motor Freight.[64] It was announced on 6 May 2011 that the two had become engaged.[65] On 9 October 2011, Lennon's birthday, McCartney and Shevell were married at Old Marylebone Town Hall where his first wedding took place in 1969. The couple attended Yom Kippur synagogue services prior to the wedding, out of respect for Shevell's Jewish faith,[66] but did not seek a religious blessing for their union.[67] Upon their marriage, Shevell became Lady McCartney.[68] McCartney wrote the song "My Valentine", from his 2012 album Kisses on the Bottom, about Shevell. She is second cousin to broadcast journalist Barbara Walters.[69]